Dean and Castiel's Guide to Matchmaking
by Amy-the-mystery-writer
Summary: Instead of Sam and Gabriel setting up Dean and Cas. What if it was the other way around? Dean, tired of his brother being alone, decides it's time to ask Castiel if Sam's got an angel soul mate. Despite the answers, he's determined to set them up.


"I believe your brother is lonely," Castiel mentioned off hand in the car.

Dean looked up from Cas's stomach, "You're really bringing that up now?"

"His soul cried out particularly hard today when we left," Castiel said, "He is lonely."

"Not for trying," Dean sighed, sitting up and pulling Cas close, "I've tried hooking him up with all kinds of women, never really worked out."

"I believe he wants what you have," Cas clarified, "You have me. Perhaps Sam is wondering if there's an angel for him?"

"Well is there?" Dean asked, "Anything to get Sam smiling again. Poor kid's too serious for his own good."

"I'm not sure," Cas admitted, "Perhaps we'll have to wait and see."

"I hate waiting…"

* * *

They were about to storm into a house of demons when it happened. Sam and Dean opened the door, saw a flash of blinding light, and were on a beach.

"What the hell?" Dean looked at the sand, "What just happened?"

"I don't know," Sam looked just as confused, "Did the demons get us?"

"Try again."

Gabriel walked up to them wearing shorts and a vibrant button up.

"What are you doing?" Dean demanded, "We were about to kill those demons!"

"You were about to get yourselves killed," Gabriel corrected, "And trust me, dying is that last thing you mutton-heads wanna do."

"Yeah?" Dean asked, "Why's that?"

"Because the entire host of heaven is looking for you," Castiel appeared next to the archangel, "Heaven is their home ground. They would have an extreme advantage over you."

"So it's for our own protection that we don't die," Dean recapped, "I get that. Why take us all the way to… here?"

"I've been watching you two," Gabriel said, snapping a fruity drink in hand, "You two have been working your little asses off, haven't you? Saving people and trying to stop the end of the world. Even the best need a break."

"Not us," Dean countered.

"We don't have time to relax," Sam said, "We've got to find a way to stop Lucifer before he destroys the world."

"He's gonna still be there when you get back," Gabriel said, "Unless his vessel explodes. Then he'll just be a glowing light. Just like Michael. Just… trust me. Armageddon can wait a few days, can't it? Tell me, honestly, when was the last time either of you had a full night sleep?"

Dean and Sam refused to look at each other.

"My point exactly," Gabriel smirked, snapping his fingers, "So stay here a few days, rest up, and then you can go back to your whole saving-the-world business."

Dean looked down and blushed in fury and embarrassment. Gabriel had snapped away all their clothes except for a skimpy speedo. Well, he got a speedo. Sam got comfortable looking trunks.

"Gabriel!" Dean shouted.

* * *

Cas cornered Dean that night. The sun had long since set, Gabriel popped in a couple of beach houses, and Dean just got out of the shower. A really nice hot shower with a massage head. He was looking forward to sleeping in an empty room with a comfortable bed knowing that Sam had one of his own the next house over, but that's when Cas cornered him.

"I've found Sam's angel," he greeted.

"We've gotta work on your hellos," Dean rolled his eyes, moving to the dresser and pulling out a pair of boxers and a t-shirt, "Okay, I'll bite. Who's the angel?"

"Gabriel."

"Heh, maybe you are getting a sense of humor."

"I'm serious, Dean. Gabriel is your brother's angel."

Dean turned around, hair ruffled from his shirt, "Wait, wait, wait. Are you- are you telling me that Gabriel, dick archangel Gabriel who killed me a thousand times and locked us in TV land is Sam's angel?"

"Yes," Cas groaned, "I don't understand how my sentence was confusing. I tried to be as simple as possible-"

"Yeah, yeah, we'll get to that later," Dean waved his hand, "Are you sure? I am not setting up my little brother with a dick angel because you got it wrong."

"I am certain," Castiel nodded, "Gabriel didn't bring us here just for a relaxing vacation. He wanted to make sure that Sam was doing well. He's always been looking out for your brother, teaching him lessons. I admit, he made poor decisions in doing so, but he cares for Sam in his own way."

"Great, that's one half of the happy couple, what about Sam?"

"Sam has wanted his help since you first met him. When you discovered his true identity, Sam no longer prayed to God. He prayed to Gabriel."

"No shit?"

"I don't-"

"Let's pretend that you're right-"

Castiel huffed.

"Okay, you ___are_ right. If Sam and Gabriel are meant for each other… don't you think they're going to need some help? I mean, call me crazy, but I don't think Sam is gonna read the signs right."

"Are you saying we push them towards each other? Romantically?"

"I'm saying we set them up," Dean smirked, "Let's play matchmaker Cas."

* * *

Once Cas got the idea of matchmaking, he was actually really good at it. He came up with all kinds of excuses to leave Sam and Gabriel on their own, taking Dean away for some reason or other, but never leaving the island.

"Oh Sam, I'd love to, but Cas and I were gonna go see some coral reef out there, maybe Gabriel…?"

"I don't believe I can help with dinner Sam. I apologize but Dean was complaining about sand and requested my help-"

"You know, I'm beat. I think I'm gonna pass on the movie. You have fun though."

Despite all this, Sam and Gabriel still weren't doing anything! Sure, they hung out a lot and starting having their own inside jokes, but it was nothing more than that. Dean complained to Cas about it all the time.

"I'm supposed to be the emotionally stunted one here," he said, "Sammy's all ___open_ and ___in-touch_ with his feelings. Why doesn't he do something about it?"

"Perhaps he would feel guilty about starting a relationship with an angel you hate so much?" Cas mentioned, his hand trailing down Dean's chest, "You aren't exactly close with Gabriel, perhaps Sam values your opinion more than Gabriel?"

"What should I do then?" Dean asked, grabbing Cas's hand and lacing their fingers together, "How am I suppose to convince Sam that he and Gabe are an okay thing in my book?"

"I have an idea," Castiel said, leaning in to kiss Dean, "But you're not going to like it."

"Lay it on me," Dean kissed Cas back.

"Be friends with Gabriel."

Dean was out the door in an instant.

* * *

He may not like the idea, but Cas had a good point. He hadn't been exactly welcoming to the archangel (because said angel is a dick). Maybe warming up to him would be for the best. On the "Let's hook up Sam with an archangel" front at least. So, begrudgingly, Dean suggested he and Gabriel build a couple of sand castles or some shit like that. Gabriel complied easily and they left Sam and Cas to be nerds together.

"I've been trying to corner you for a while now," Gabriel said ominously.

___Fuck_, "Why?"

"Big brother talk of course," Gabriel grinned, "You're banging Cas and even if I left heaven a long time ago, doesn't change the fact that I'm his big bro and you need the fear of God in you."

Dean didn't say anything, just stared at Gabriel with his mouth wide open.

"Don't worry," Gabriel patted his shoulder, "I don't think Dad is gonna smite you because of this. But you gotta remember Cas is an angel and he thinks the fucking world of you. So you don't screw this up, got it?"

Dean nodded meekly. The mood took a sudden change as Gabriel starting talking about some of the various pranks he pulled when he was hiding as the trickster. Dean remembered when they first met, and he remembered that he thought the man had style. Those pranks at the college were gold. Slow dancing alien? Priceless.

Not to be outdone, Dean told of his own prank wars he and Sam used to get into. They always had to stop before someone got seriously hurt, because their pranks went from harmless to deadly within days. Gabriel was impressed. Going so far as to say "I knew there was a reason I liked you boys."

Sam was waiting for them at the beach houses, looking worried, though for who Dean couldn't tell. Sam sighed, relieved that both of them were still alive, before doing a double take. Were they actually laughing together?

"Aw man Sam," Dean said, "You should hear his stories."

"I have," Sam said slowly, "What's up with this?"

"Deano here thought he'd give me a chance," Gabriel said smoothly, "Since I did give you this awesome vacation time."

"And he didn't try to kill your or anything?" Sam said slowly, "Or the other way around?"

"Yeah, come on Sammy, have a bit of faith," Dean clapped his brother's shoulder and walked up to Cas.

Sam was still confused, but took it all in stride, taking Gabriel aside. As they talked Sam's face lit up like the sun. Dean grinned. This was worth it.

* * *

It was getting time to head back to the real world, and Sam and Gabriel ___still_ haven't done anything. Dean was getting really impatient. He was thinking of just locking them in a closet or something until they figured things out. Cas didn't approve.

"Come on Sammy, we got a world to save," Dean announced himself as he walked into Sam's beach house.

Sam was sprawled out on his bed, blanket just covering his waist, eyes closed and mouth slightly open. Dean was gonna call him out on it when Gabriel poked his head out from the covers.

"Bad timing, Deano," the archangel said.

"Oh- oh!" Dean shouted, "Put a sock on the door next time!"

He huffed and went outside where his own angel was waiting.

"I assume it went well?" Cas smirked.

"I need you to erase that image from my mind, forever," Dean said, "Come on man, hit me with your mojo."

"No," Castiel shook his head, "You should have known better. Consider it a lesson learned."

"I hate you."

"I know."

Dean smiled and kissed Cas, "Well since they aren't moving any time soon, care for some beach sex?"

"Of course."


End file.
